The National Road - Maryland - US 40A: Middletown and Boonsboro

Just west of Frederick,
Route 40 splits in two, the old road and the new road. If you bear left
and take US 40A, you will be on the old road. Alternate Route 40 through
Frederick and Washington Counties bridges centuries of American History.
Taverns and towns that are over 250 years old and mountain passes that
were of strategic importance during the Civil War can be found along the over
25 miles of this "old" road.

Middletown is a small village of nearly
4,000 residents sitting near the base of the South Mountains west of Frederick.
Middletown was in the center of activity during the days before the battle
of Antietam. In 1862, Union and Confederate forces in the early September
days leading to Antietam would march along the National Road through the
town. The old National Road crosses South Mountain at a point called
Turner's Gap. It was
at Turner's Gap, along with nearby Fox and Crampton's Gap, that the Battle of South Mountain was waged on September 14, 1862. The battle
which was a Union victory is called by some the "Prelude to Antietam" which
would occur three days later near Sharpsburg. At Turner's Gap, there
are six cast iron tablets describing the battle which were placed along
the National Road in 1897. The tablets were moved to a safer distance
from the road in 1987. (1)

The Old South Mountain
Inn (Adam Prince)

In addition to being a battle site in the Civil War, there is plenty more history at Turner's
Gap. First, the Appalachian
Trail crosses the old National Road here. Standing nearby is the Old South Mountain Inn which has seen plenty of history since it was built in
1732. Many dignitaries in early-American history once stayed here.
Including Henry Clay, who many consider as the father of the National Road.
The tavern was commandeered by John Brown's militia before his raid on
Harpers Ferry. During the Battle of South Mountain, it served as
headquarters for Confederate General D. H. Hill. Today, the tavern
is well known throughout the area for its fine dining and American cuisine.
(2)

Dahlgren Chapel
(Adam Prince)

Across from the tavern and bordered by
the Appalachian Trail is Dahlgren Chapel. The chapel is named for and was built by Sarah
Madeleine Vinton Dahlgren in 1881. Mrs. Dahlgren who was a noted
author, purchased what is now the Old South Mountain Inn in 1876 and transformed
it into a private residence. She built the chapel as a Catholic Church.
Gothic in design, the chapel today can be used for weddings and private
services. (3)

The National Road
through Boonsboro (Doug Kerr).

Sitting west of Turner's Gap is the town
of Boonsboro. The National
Road through Boonsboro has historical significance as a 10 mile section
of the road was the first to be built with a macadam surface in 1823. The process, named for John Loudon McAdam, greatly
improved the quality of the National Road and by 1830, 73 miles of the
highway had been converted to a macadamized surface. (4) Boonsboro
has the distinct honor of being the first town or city in America to dedicate
a monument to George Washington. The stone tower was built by residents
in one day on July 4, 1827. The monument is located off of the National
Road and is part of Washington Monument State Park.

The Boonsboro Historic District is listed in the National Register of Historic Places and consists of much of Main Street. Many of the buildings along Main Street (US 40A) date back to the National Road's peak period of 1820-1850. The historic district has been listed on the register since 2005. Some additional photos of some of the historic buildings within Boonsboro are below.

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